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Schooner Woodwind

80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
Review Highlights
Amazing ride, amazing crew!

This is my second time riding on the Schooner Woodwind. I came previously on a bachelorette party... read more

Reviewed 1 week ago
Sarah I
Washington DC, District of Columbia
via mobile
Amazing Ride!

My wife and I recently went on Woodwind for the sunset cruise and boat and breakfast. The sunset... read more

Reviewed 3 weeks ago
Baltimore, Maryland
Read all 228 reviews
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The classic, wooden 74' Schooner Woodwind sails multiple cruises daily (in season) for public and private charters. Up to 48 passengers on each of our twin schooners. Whether a couple, family, party or corporate, we can accommodate you. We also have a Boat & Breakfast available (in season) on Saturdays. Come Sail Away!
  • Excellent84%
  • Very good11%
  • Average2%
  • Poor1%
  • Terrible2%
Travellers talk about
“sunset cruise” (29 reviews)
“hour sail” (14 reviews)
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Hours Today: 10:00 - 18:30
80 Compromise St, Annapolis Marriott Waterfront Hotel, Annapolis, MD 21401-1810
+1 410-263-7837
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Reviews (228)
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1 - 10 of 228 reviews

Reviewed 1 week ago via mobile

This is my second time riding on the Schooner Woodwind. I came previously on a bachelorette party, and enjoyed myself in both settings. The crew is accommodating and informative. The views are spectacular. It's a perfect price for the experience. Highly recommend the sunset sail!...More

1  Thank Sarah I
Reviewed 3 weeks ago

My wife and I recently went on Woodwind for the sunset cruise and boat and breakfast. The sunset cruise was amazing, the staff was amazing, and the view of Annapolis from the boats path was breathtaking. The boat and breakfast was hosted by Captain Jen...More

1  Thank AW0710
Reviewed 4 weeks ago

Perfect chance to stay cool and see the sights without doing the work. If you are a sailor this is a kiddie ride. If you are a sightseer it is only 2 hours but packed with much fun.

Thank fclarkeiv
Reviewed 4 weeks ago

Decided to book a sunset sail. Tickets were bought a few days in advance.. It was a very cool and cloudy evening. The sail was delightful even though the weather was not. The crew was extremely accommodating and knowledgeable which made for a lovely evening....More

Thank cesloan2
Reviewed 17 May 2017 via mobile

Great tour out on the water and enjoyable day. A little expensive but overall makes for a fun day out on the water in Annapolis(which is the way you need to see annapolis). Fun crew and they give you alcohol, what could be better

Thank vacaexpert777
Reviewed 3 May 2017

My husband and I had been wanting to go on a sail boat for a while now, we finally found a location and price we were happy with. The only issue was that the boat didn't go far, for a 2 hour sail we stayed...More

Thank FFXTravelers
Bill M, Manager at Schooner Woodwind, responded to this reviewResponded 5 May 2017

Hello FFXTravelers, Thank you for choosing the Schooner Woodwind for your first sailing experience. Sailing is a different experience with Mother Nature every time you step aboard. We offer a true sailing experience in the two hours that we have our guests on board. On...More

Reviewed 8 October 2016

I've done this twice now in my two visits to Annapolis. Enjoyed a beautiful sunset sail both times. In July, the boat was full, but everyone had a place to sit. In October, there was plenty of room to move about, if that's your thing....More

1  Thank EPBOL
Reviewed 18 September 2016

Beautiful afternoon trip on one of two tall masted schooners. The crew were very fun and professional. They took us out on the bay for about an hour and a half. Very family friendly event. Beautiful views of Annapolis harbor and the bay.

1  Thank FunlovingJohn
Reviewed 17 September 2016 via mobile

As stated in other reviews the boats are overcrowded, to the point they feel unsafe at times. If you are near the end of the line you will get stuck in the middle of the boat, below the advertising tarp, with no breeze. The captain...More

Thank John P
BethLeath, Manager at Schooner Woodwind, responded to this reviewResponded 21 September 2016

I am so sorry to hear that you hated the cruise. I looked at the comment cards that were handed back to us by over 90% of the guests on the boat and cruise you were on. No one else had the same experience as...More

Reviewed 12 September 2016

We took the 5.30pm Sun Set tour on Woodwind. There was little wind but we still had a look into creeks and secret places around Chesapeake Bay near Annapolis. As the sun went down we returned to Annapolis to get beautiful pictures. Interesting history from...More

Thank hanskraay
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Questions & AnswersAsk a question
Kimbercat S
I am really interested in sailing but have never been. My goal is to one day live aboard and travel. Will there be an opportunity to learn some sailing tips on the two hours trip? Also can the trip accommodate a heavier person (350 lb.) with no mobility issues?
6 June 2016|
Answer Show all 2 answers
Response from Bill M | Property representative |
Guests have the opportunity to help raise the sails, steer the schooner, and ask questions. You also can just sit back and relax! Captain may have suggestions of where best to take a lesson locally. Weight is not an issue... More
Do you have sailing trips on Labor Day? Time? Price?
2 September 2015|
Answer Show all 3 answers
Response from BethLeath | Property representative |
Thank you for your question. Yes we are sailing on Labor Day from 10am-12pm, 12:30-2:30pm, 3-5pm & 5:30-7:30pm. The cost is $44/adult, $42/senior (over 60) & $27/child (under 12). Please visit our website to purchase... More
Hi, I am thinking about this activity for my grandsons aged 3 and 9. How well do active 3 year olds do on the boat and is it allowed?
1 July 2015|
Answer Show all 8 answers
Response from 2118burke | Reviewed this property |
There is another nice boat out of Annapolis - it's a Priate Ship - specifically for kids. They dress up and it's great for small children. The Windwood for the evening cruise was mostly adults so not sure about daytime... More